Dihydromyrcenol defined according to the structure: ##STR2## was heretofore produced commercially by means of: (i) hydrogenating .alpha.-pinene to form .alpha.-pinane;
(ii) pyrolyzing the .alpha.-pinene to form .alpha.-pinane pyrolyzate containing a mixture of hydrocarbons; PA0 (iii) carefully distilling the resulting .alpha.-pinane pyrolyzate in order to obtain dihydromyrcene of a very high purity, dihydromyrcene having the structure: ##STR3## (iv) reacting the dihydromyrcene with hydrogen chloride in order to form dihydromyrcenyl chloride defined according to the structure: ##STR4## and then (v) hydroxylating the resulting dihydromyrcenyl chloride to form dihydromyrcenol having the structure: ##STR5## PA0 (i) can first be hydrohalogenated in the presence of an acid catalyst, e.g., a Lewis acid or protonic acid catalyst; and then PA0 (ii) the resulting mixture of tertiary halides can be, en masse, hydroxylated with water or acetoxylated with acetic acid using one or more of a specific group of hydroxylation or of acetoxylation catalysts whereby the only tertiary alcohol (or acetate thereof) formed is dihydromyrcenol (or its acetate) and whereby other materials which are formed are merely hydrocarbons which can easily, economically and quickly be separated from said dihydromyrcenol (or its acetate).
Thus, U.S. Pat. No. 2,902,510, at Example VIII discloses the reaction of dihydromyrcene with hydrogen chloride gas in order to form, in 95-98% yields, dihydromyrcenyl chloride according to the reaction: ##STR6##
In Example IX of U.S. Pat. No. 2,902,510 the resulting dihydromyrcenyl chloride is reacted with water, in the presence of calcium hydroxide in order to form, in 65-70% yields, dihydromyrcenol according to the reaction: ##STR7##
The reaction of tertiary terpenyl halides with water to form tertiary terpenols, specifically .alpha.-terpeneol is disclosed in Anandaraman, et al, Tetrahedron Letters, Vol. 21, pages 2189-2190, (1980) and in Gurudutt, et al, Tetrahedron, Vol. 38, No. 12, pages 1843-1846.
Thus, Anandaraman, et al, discloses the reactions: ##STR8## and indicates that the attempted reaction of a secondary halide to form its corresponding alcohol does not take place when using zinc salts or zinc oxide as hydroxylation catalysts, to wit: ##STR9## Gurudutt, et al, indicates that the following reaction can take place: ##STR10##
Furthermore, a technique for formation of the .alpha.-pinane pyrolyzate is set forth in U.S. Pat. No. 2,902,495 issued on Sept. 1, 1959, the specification for which is incorporated by reference herein.
Nothing in the prior art, however, indicates that the entire .alpha.-pinane pyrolyzate or a mixture containing the components thereof produced in any other manner: